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First Total Synthesis of (−)‐Ligustiphenol
Author(s) -
Luo Huan,
Liu Yanfei,
Liang Dong,
Hao Zhiyou,
Wang Yan,
Zhang Chunlei,
Zhang Qingjian,
Yu Dequan
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200630
Subject(s) - chemistry , steric effects , total synthesis , adduct , nucleophile , stereochemistry , nucleophilic addition , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis
The first asymmetric total synthesis of (−)‐ligustiphenol is reported. The key step was conducted by exploiting a steric hindrance effect to control the formation of the adduct in a nucleophilic α ‐Li‐phenolate addition reaction to the intermediate α ‐oxo (−)‐menthyl ester. The synthesis is concise and feasible for the construction of analogous compounds and investigation of their biological activity.